Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.

Takaaki Kubota; Ken'Ichi Kura; Jane Fromont; Jun'Ichi Kobayashi

doi:10.1016/j.tet.2012.10.062

Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.

Takaaki Kubota, Ken'Ichi Kura, Jane Fromont, Jun'Ichi Kobayashi

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an α,β-unsaturated 3,5-disubstituted γ-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells.

Original language	English
Pages (from-to)	96-100
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.062
Publication status	Published - Jan 7 2013
Externally published	Yes

Keywords

Amphimedon sp.
Bis-3-alkylpyridine alkaloid
Cytotoxicity
Marine sponge
Pyrinodemins G-I

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.tet.2012.10.062

Cite this

@article{dfcd6f95d4174cb787c43e708dec6606,

title = "Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.",

abstract = "Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an α,β-unsaturated 3,5-disubstituted γ-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells.",

keywords = "Amphimedon sp., Bis-3-alkylpyridine alkaloid, Cytotoxicity, Marine sponge, Pyrinodemins G-I",

author = "Takaaki Kubota and Ken'Ichi Kura and Jane Fromont and Jun'Ichi Kobayashi",

note = "Funding Information: We thank Mr. Z. Nagahama for his help with sponge collection, and Ms. S. Oka, Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University, for measurements of ESIMS. This work was supported by the Akiyama Life Science Foundation, the Suhara Memorial Foundation, and Grant-in-Aid for Scientific Research on Innovative Areas (Biosynthetic Machinery) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan . ",

year = "2013",

month = jan,

day = "7",

doi = "10.1016/j.tet.2012.10.062",

language = "English",

volume = "69",

pages = "96--100",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.

AU - Kubota, Takaaki

AU - Kura, Ken'Ichi

AU - Fromont, Jane

AU - Kobayashi, Jun'Ichi

N1 - Funding Information: We thank Mr. Z. Nagahama for his help with sponge collection, and Ms. S. Oka, Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University, for measurements of ESIMS. This work was supported by the Akiyama Life Science Foundation, the Suhara Memorial Foundation, and Grant-in-Aid for Scientific Research on Innovative Areas (Biosynthetic Machinery) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan .

PY - 2013/1/7

Y1 - 2013/1/7

N2 - Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an α,β-unsaturated 3,5-disubstituted γ-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells.

AB - Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an α,β-unsaturated 3,5-disubstituted γ-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells.

KW - Amphimedon sp.

KW - Bis-3-alkylpyridine alkaloid

KW - Cytotoxicity

KW - Marine sponge

KW - Pyrinodemins G-I

UR - http://www.scopus.com/inward/record.url?scp=84870060497&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84870060497&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.10.062

DO - 10.1016/j.tet.2012.10.062

M3 - Article

AN - SCOPUS:84870060497

SN - 0040-4020

VL - 69

SP - 96

EP - 100

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this